Category: 115652-52-3

Adding a certain compound to certain chemical reactions, such as: 115652-52-3, (1-Aminocyclopropyl)methanol hydrochloride, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 115652-52-3, blongs to alcohols-buliding-blocks compound. HPLC of Formula: C4H10ClNO

[l-[(5-Bromo-4-chloro-3-pyridyl)methylamino]cyclopropyl]methanol:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115652-52-3, its application will become more common.

Reference:
Patent; DENALI THERAPEUTICS INC.; DE VICENTE FIDALGO, Javier; ESTRADA, Anthony A.; FENG, Jianwen A.; FOX, Brian; FRANCINI, Cinzia Maria; HALE, Christopher R.H.; HU, Cheng; LESLIE, Colin Philip; OSIPOV, Maksim; SERRA, Elena; SWEENEY, Zachary K.; THOTTUMKARA, Arun; (226 pag.)WO2018/213632; (2018); A1;,
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Related Products of 115652-52-3 ,Some common heterocyclic compound, 115652-52-3, molecular formula is C4H10ClNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a mixture of 2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylpropanoic acid (40 mg, 0.1 mmol) , (1-aminocyclopropyl) methanol hydrochloride (16 mg, 0.13 mmol) , DIPEA (60 mg, 0.46 mmol) in DMF (1 mL) was added HATU (50 mg, 0.13 mmol) at rt and the mixture was stirred at rt for 3 hrs. The mixture was diluted with 15 mL of EtOAc, washed with brine (5 mL x 3) , dried over Na 2SO 4, concentrated and the resulted oil was purified by prep-TLC (EtOAc: 100%) to give the title product (28.0 mg, yield: 61%) after lyophilization. 1H NMR (400 MHz, DMSO-d6) delta 8.22 (s, 1H) , 8.10 -7.82 (m, 3H) , 7.75 (s, 1H) , 7.35 -7.19 (m, 4H) , 7.11 (d, J = 8.0 Hz, 2H) , 6.79 -6.69 (m, 1H) , 4.55 (t, J = 5.6 Hz, 1H) , 3.59 (dd, J = 11.2, 6.0 Hz, 1H) , 3.41 (dd, J = 11.2, 5.6 Hz, 1H) , 2.25 (s, 3H) , 0.73 -0.50 (m, 4H) . MS: M/e 459 (M+1) +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115652-52-3, its application will become more common.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; ZHOU, Changyou; (152 pag.)WO2019/196803; (2019); A1;,
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Electric Literature of 115652-52-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 115652-52-3, name is (1-Aminocyclopropyl)methanol hydrochloride. A new synthetic method of this compound is introduced below.

Intermediate: 5-((5-((3′-(3-bromopropoxy)-2′-chloro-2-methyl-[1,1′-biphenyl]-3-yl)methoxy)-4-chloro-2-(((1-(hydroxymethyl)cyclopropyl)amino)methyl)phenoxy)methyl)nicotinonitrile To a solution of 5-((5-((3′-(3-bromopropoxy)-2′-chloro-2-methyl-[1,1′-biphenyl]-3-yl)methoxy)-4-chloro-2-formylphenoxy)methyl)nicotinonitrile (20 mg, 0.031 mmol) in a mixture of 1,2-dichloroethanel (0.8 mL) and EtOH (0.5 mL) was added (1-aminocyclopropyl)methanol, HCl (12 mg, 0.097 mmol), acetic acid (3 muL, 0.052 mmol), and 4 A mol sieves. The reaction was flushed briefly with N2, capped, stirred at room temp for 90 min, then treated dropwise (over 1 h) with sodium cyanoborohydride, 1.0M in THF (65 muL, 0.065 mmol) and stirred at room temp for 18 h. Additional sodium cyanoborohydride (15 mulit) was added dropwise and the reaction was stirred at room temp for 1 h. N,N-diisopropylethylamine (15 muL) was added and the reaction stirred at room temp for 1.5 h. The solvent was removed under a gentle stream of N2 to give the title compound that was used “as is” without purification in subsequent reactions. LC/MS Condition A: ret time 1.18 min; m/e=710(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,115652-52-3, (1-Aminocyclopropyl)methanol hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, KAP-SUN; Connolly, Timothy P.; Frennesson, David B.; Grant-Young, Katharine A.; Hewawasam, Piyasena; Langley, David R.; Meng, Zhaoxing; Mull, Eric; Parcella, Kyle E.; Saulnier, Mark George; Sun, Li-Qiang; Wang, Alan Xiangdong; Xu, Ningning; Zhu, Juliang; Scola, Paul Michael; (511 pag.)US2017/107202; (2017); A1;,
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Electric Literature of 115652-52-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 115652-52-3 as follows.

Example 1Synthesis of: (/?)-3-((/?)-2-amino-3-(l-(hvdroxymethyl)cvclopropylamino)-3-oxopropylthio) propane- 1,2-diyl didodecanoateStep 1: (R)-3-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(l-(hydroxymethyl)cyclo- propylamino)-3-oxopropylthio)propane-l,2-diyl didodecanoate[000398] To a solution of (5«,9«)-9-(dodecanoyloxy)-l-(9H-fluoren-9-yl)-3,12-dioxo-2,l l- dioxa-7-thia-4-azatricosane-5-carboxylic acid (6, 1 eq) and HBTU (1.2 eq) in DCM (0.06 M) was added DIEA (3.5 eq), followed by (1-aminocyclopropyl) methanol hydrochloride (1.2 eq). The reaction was stirred at room temperature for 2 hours. The crude mixture was purified by flash chromatography on a COMBIFLASH system (ISCO) using 30-50% EtO Ac/Hex to give (R)-3- ((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(l-(hydroxymethyl)cyclopropylamino)-3- oxopropylthio)propane- 1 ,2-diyl didodecanoate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115652-52-3, its application will become more common.

Reference:
Patent; IRM LLC; WU, Tom Yao-Hsiang; ZOU, Yefen; HOFFMAN, Timothy Z.; PAN, Jianfeng; WO2011/119759; (2011); A1;,
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Synthetic Route of 115652-52-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 115652-52-3 as follows.

8.3 [1-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-cyclopropyl]-methanol (III-4) 1.4 g (II) are placed in 10 ml dioxane, first 3.6 ml diisopropylethylamine, then 1 g of 1-aminocyclopropanmethanol (see 8.2) are added. The reaction mixture is heated to 160 C. until there is no further reaction and after cooling evaporated down. The residue is treated with cyclohexane/ethyl acetate (8:2) in the ultrasound bath and the solid is suction filtered and dried. 1.24 g (III-4) are obtained as a solid. Analytical HPLC-MS (method A): RT=1.01 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115652-52-3, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; Nickolaus, Peter; US2013/237527; (2013); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts